Dronabinol

{{Short description|Generic name of Δ9-THC in medicine}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Distinguish|Droperidol}} {{About|tetrahydrocannabinol in the pharmaceutical context|more information about this substance|Tetrahydrocannabinol}} {{Infobox drug | drug_name = Dronabinol | image = THC.svg | image_class = skin-invert-image | image2 = Delta-9-tetrahydrocannabinol-from-tosylate-xtal-3D-balls.png | image_class2 = bg-transparent | tradename = Marinol, Syndros | licence_US = Dronabinol | legal_US = Schedule II as Syndros, Schedule III as Marinol | legal_status = SE: Förteckning II | dependency_liability = Physical: Low Psychological: Low–moderate | addiction_liability = Relatively low{{citation needed|date=March 2025}} | routes_of_administration = By mouth | bioavailability = {{abbrlink|PO|Oral administration}}: 6–20% | onset = {{abbr|PO}}: 0.5–1 hour | elimination_half-life = 25–36 hours | duration_of_action = {{abbr|PO}}: 4–6 hours | synonyms = (−)-trans-Δ9-tetrahydrocannabinol | class = Cannabinoid

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 1972-08-3 | ATC_prefix = A04 | ATC_suffix = AD10 | PubChem = 16078 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 66964 | IUPHAR_ligand = 2424 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00470 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 15266 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7J8897W37S | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00306 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 465

| IUPAC_name = (6a''R'',10a''R'')-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6''H''-benzo[''c'']chromen-1-ol | C = 21 | H = 30 | O = 2 | SMILES = CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CYQFCXCEBYINGO-IAGOWNOFSA-N

| boiling_point = 155–157 | boiling_notes = 0.05mmHg,<ref>{{cite journal| vauthors = Gaoni Y, Mechoulam R |title=Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish|journal=Journal of the American Chemical Society|date=April 1964|volume=86|issue=8|pages=1646–47|doi=10.1021/ja01062a046|bibcode=1964JAChS..86.1646G }}</ref> 157–160°C @ 0.05mmHg<ref>{{cite journal| vauthors = Adams R, Cain CK, McPhee WD, Wearn RB |title=Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols|journal=Journal of the American Chemical Society|date=August 1941|volume=63|issue=8|pages=2209–13|doi=10.1021/ja01853a052|bibcode=1941JAChS..63.2209A }}</ref> | solubility = 0.0028 | sol_units =  mg/mL (23 °C)<ref name='Garrett1974'>{{cite journal | vauthors = Garrett ER, Hunt CA | title = Physiochemical properties, solubility, and protein binding of delta9-tetrahydrocannabinol | journal = Journal of Pharmaceutical Sciences | volume = 63 | issue = 7 | pages = 1056–64 | date = July 1974 | pmid = 4853640 | doi = 10.1002/jps.2600630705 | bibcode = 1974JPhmS..63.1056G }}</ref> | specific_rotation = −152° (ethanol) }}{{Cannabis sidebar}}

'''Dronabinol''' ({{Abbrlink|INN|International Nonproprietary Name}}), sold under the brand names '''Marinol''' and '''Syndros''', is the generic name for the molecule of '''(−)-trans-Δ9-tetrahydrocannabinol''' ('''THC''') in the pharmaceutical context. It has indications as an appetite stimulant and antiemetic and is approved by the US Food and Drug Administration (FDA) as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting.<ref name="fda">{{cite web|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018651s021lbl.pdf|title=Marinol (Dronabinol)|date=September 2004|publisher=US Food and Drug Administration|access-date=14 January 2018}}</ref><ref>{{cite web|url=http://www.cancer.gov/cancertopics/pdq/cam/cannabis/patient/page2|title=Cannabis and Cannabinoids|publisher=National Cancer Institute|access-date=12 January 2014|date=2011-10-24}}</ref><ref>{{cite journal | vauthors = Badowski ME | title = A review of oral cannabinoids and medical marijuana for the treatment of chemotherapy-induced nausea and vomiting: a focus on pharmacokinetic variability and pharmacodynamics | journal = Cancer Chemotherapy and Pharmacology | volume = 80 | issue = 3 | pages = 441–449 | date = September 2017 | pmid = 28780725 | pmc = 5573753 | doi = 10.1007/s00280-017-3387-5 }}</ref>

Dronabinol is the principal psychoactive constituent enantiomer form, (−)-''trans''-Δ9-tetrahydrocannabinol, found in ''Cannabis sativa'' L. plants,<ref>{{cite web|url=https://www.incb.org/incb/en/psychotropics/green-list.html|title=List of psychotropic substances under international control|website=International Narcotics Control Board|access-date=25 April 2018|quote=This international non-proprietary name refers to only one of the stereochemical variants of delta-9-tetrahydrocannabinol, namely (−)-trans-delta-9-tetrahydrocannabinol}}</ref> but can also be synthesized in the laboratory. Dronabinol does not include any other tetrahydrocannabinol (THC) isomers or any cannabidiol (CBD).

==Medical uses== ===Low appetite and nausea=== Dronabinol is used to stimulate appetite and therefore weight gain in patients with HIV/AIDS and cancer. It is also used to treat chemotherapy-induced nausea and vomiting.<ref name=canabisfun>{{cite journal | vauthors = Badowski ME, Yanful PK | title = Dronabinol oral solution in the management of anorexia and weight loss in AIDS and cancer | journal = Therapeutics and Clinical Risk Management | volume = 14 | pages = 643–651 | date = 2018 | pmid = 29670357 | pmc = 5896684 | doi = 10.2147/TCRM.S126849 | doi-access = free }}</ref><ref name="Brafford 2016">{{cite journal | vauthors = May MB, Glode AE | title = Dronabinol for chemotherapy-induced nausea and vomiting unresponsive to antiemetics | journal = Cancer Management and Research | volume = 8 | pages = 49–55 | year = 2016 | pmid = 27274310 | pmc = 4869612 | doi = 10.2147/cmar.s81425 | publisher = Informa PLC | doi-access = free }}</ref>

===Pain=== Dronabinol demonstrated analgesic efficacy in a majority of studies in chronic pain, the data in acute pain is less conclusive.<ref name=pain>{{cite journal |vauthors=de Vries M, van Rijckevorsel DC, Wilder-Smith OH, van Goor H | title=Dronabinol and chronic pain: importance of mechanistic considerations. |date=2014 |journal=Expert Opinion on Pharmacotherapy | volume=15 | issue=11 | pages=1525–34 | doi=10.1517/14656566.2014.918102 |pmid=24819592| s2cid=31008562 }}</ref>

===Cannabis use disorder=== There is incomplete evidence for the utility of dronabinol in cannabis use disorder, but it does not appear to be effective.<ref>{{cite journal | vauthors = Spiga F, Parkhouse T, Tang VM, Savović J, Le Foll B, Nielsen S | title = Pharmacotherapies for cannabis use disorder | journal = The Cochrane Database of Systematic Reviews | volume = 9 | issue = 9 | article-number = CD008940 | date = September 2025 | pmid = 41025421 | pmc = 12481667 | doi = 10.1002/14651858.CD008940.pub4 }}</ref>

===Sleep apnea=== Limited human studies suggest dronabinol may improve sleep apnea scores.<ref name="Schütz 2021">{{cite journal |vauthors=Schütz SG, Dunn A, Braley TJ, Pitt B, Shelgikar AV |date=June 2021 |title=New frontiers in pharmacologic obstructive sleep apnea treatment: A narrative review |journal=Sleep Medicine Reviews |publisher=Elsevier BV |volume=57 |doi=10.1016/j.smrv.2021.101473 |pmid=33853035 |s2cid=233242139 |quote="Initial rodent studies showed that injections of dronabinol, a synthetic form of delta-9-tetrahydrocannabinol, in the nodose ganglia suppressed serotonin induced reflex apneas and increased upper airway dilating muscle activity during sleep. Limited studies in humans with moderate-to-severe OSA have demonstrated significant reduction in AHI with dronabinol use." |article-number=101473}}</ref> Phase 2B clinical trials were completed in 2017 for FDA approval for this indication.<ref>{{Cite news|url=http://www.sleepreviewmag.com/2017/01/drug-dronabinol-reduces-symptoms-obstructive-sleep-apnea-finds-phase-2b-study/|title=Drug Dronabinol Reduces Symptoms of Obstructive Sleep Apnea, Finds Phase 2B Study |work=Sleep Review|access-date=2018-11-04|language=en-US}}</ref><ref>{{Cite news|url=https://neurosciencenews.com/sleep-apnea-cannabis-8051/|title=Synthetic Cannabis-Like Drug Reduces Sleep Apnea|date=2017-11-29|work=Neuroscience News|access-date=2018-11-04|language=en-US}}</ref><ref>{{Cite journal| vauthors = Carley DW, Prasad B, Reid KJ, Malkani R, Attarian H, Abbott S, Vern B, Xie H, Yuan C, Zee PC |date=2017-04-28|journal=Journal of Sleep and Sleep Disorders Research |language=en|volume=40|issue=suppl_1|pages=A207–A208|doi=10.1093/sleepj/zsx050.557|issn=0161-8105|title=0558 Dronabinol Reduces Ahi and Daytime Sleepiness in Patients with Moderate to Severe Obstructive Sleep Apnea Syndrome|doi-access=free}}</ref>

==Adverse effects== Common side effects of dronabinol include euphoria, drowsiness, dizziness, decreased motor coordination, anxiety, paranoia, confusion, and a rapid heartbeat, among others.<ref>{{Cite web |title=HIGHLIGHTS OF PRESCRIBING INFORMATION: MARINOL (dronabinol) capsules, for oral use, CIII Initial U.S. Approval: 1985 |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf |archive-url=https://web.archive.org/web/20171217031410/https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf |archive-date=December 17, 2017 |website=Food and Drug Administration}}</ref>

===Overdose===

In a mild overdose of dronabinol, the typical side effects are exacerbated, whereas a severe overdose presents with lethargy, slurred speech, severe ataxia, and orthostatic hypotension.<ref name="fda" /><ref name="American Health Packaging">{{cite web|title=Dronabinol capsule (American Health Packaging) |url=https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=68b4168b-5782-4e68-a25a-5b4e4408dbce |publisher=US National Library of Medicine |access-date=12 January 2014|date=July 2012}}</ref>

==Pharmacology== {{Main|Tetrahydrocannabinol#Pharmacology}}

==History== While dronabinol was initially approved by the United States Food and Drug Administration (FDA) on May 31, 1985,<ref name="DEA Diversion Control Division 1999">{{cite web | title=1999 - Rescheduling of the Food and Drug Administration Approved Product Containing Synthetic Dronabinol [(-)-D9-(trans)-Tetrahydrocannabinol] in Sesame Oil and Encapsulated in Soft Gelatin Capsules From Schedule II to Schedule III. | website=DEA Diversion Control Division | date=1999-07-02 | url=https://www.deadiversion.usdoj.gov/fed_regs/rules/1999/fr0702.htm | access-date=2021-05-19 | archive-date=2021-05-01 | archive-url=https://web.archive.org/web/20210501230130/https://www.deadiversion.usdoj.gov/fed_regs/rules/1999/fr0702.htm }}</ref> it was not until May 13, 1986, the Drug Enforcement Administration (DEA), issued a Final Rule and Statement of Policy authorizing the "rescheduling of synthetic dronabinol in sesame oil and encapsulated in soft gelatin capsules from Schedule I to Schedule II" (DEA 51 FR 17476-78). This permitted medical use of Marinol, albeit with the severe restrictions associated with Schedule II status.<ref>51 Fed. Reg. 17476 (1986), Tuesday, May 13, 1986, pages 17476-17478</ref> For instance, refills of Marinol prescriptions were not permitted.

On April 29, 1991, the Commission on Narcotic Drugs, in accordance with article 2, paragraphs 5 and 6, of the Convention on Psychotropic Substances of 1971, decided that Δ9-tetrahydrocannabinol (also referred to as Δ9-THC) and its stereochemical variants should be transferred from Schedule I to Schedule II of that Convention. This released Δ9-THC from many of the restrictions imposed by the convention, facilitating its marketing as medication.<ref>{{Cite book| vauthors = Riboulet-Zemouli K, Krawitz MA, Ghehiouèche F |author-link2=Michael Krawitz |url=https://www.researchgate.net/publication/333825934|title=The Crimson Digest (Vol. 1), Briefing on the international scientific assessment of Cannabis: Processes, stakeholders and history|publisher=FAAAT|year=2018|isbn=979-10-97087-06-7|location=Paris|pages=37–43}}</ref>

An article published in the April–June 1998 issue of the ''Journal of Psychoactive Drugs'' found that "Healthcare professionals have detected no indication of script-chasing or doctor-shopping among the patients for whom they have prescribed dronabinol". The authors state that Marinol has a low potential for abuse.<ref name="pmid9692381">{{cite journal | vauthors = Calhoun SR, Galloway GP, Smith DE | title = Abuse potential of dronabinol (Marinol) | journal = Journal of Psychoactive Drugs | volume = 30 | issue = 2 | pages = 187–96 | year = 1998 | pmid = 9692381 | doi = 10.1080/02791072.1998.10399689 }}</ref>{{Better source needed|date=June 2011}}

In 1999, in the United States, Marinol was rescheduled from Schedule II to Schedule III of the Controlled Substances Act, reflecting a finding that dronabinol had a potential for abuse less than that of cocaine and heroin.<ref name="DEA Diversion Control Division 1999" /> This rescheduling constituted part of the argument for a 2002 petition for removal of cannabis from Schedule I of the Controlled Substances Act, in which petitioner Jon Gettman noted, "Cannabis is a natural source of dronabinol (THC), the ingredient of Marinol, a Schedule III drug. There are no grounds to schedule cannabis in a more restrictive schedule than Marinol".<ref>{{cite web |url=http://www.drugscience.org/PDF/Petition_Final_2002.pdf |title=Petition to Reschedule Cannabis (Marijuana) |date=9 October 2002 |publisher=Coalition for Rescheduling Cannabis |access-date=25 January 2018 |archive-date=8 April 2018 |archive-url=https://web.archive.org/web/20180408192822/https://www.drugscience.org/PDF/Petition_Final_2002.pdf }}</ref>{{Better source needed|date=June 2011}}

In 2003, the World Health Organization Expert Committee on Drug Dependence recommended transferring THC to Schedule IV of the convention, citing its medical uses and low abuse potential.<ref>{{cite web|url=https://www.who.int/substance_abuse/right_committee/en/index.html |archive-url=https://web.archive.org/web/20050107200642/http://www.who.int/substance_abuse/right_committee/en/index.html |archive-date=January 7, 2005 |title=WHO Expert Committee on Drug Dependence |publisher=World Health Organization |access-date=12 January 2014}}</ref> In 2019, the Committee recommended transferring Δ9-THC to Schedule I of the Single Convention on Narcotic Drugs of 1961, but its recommendations were rejected by the United Nations Commission on Narcotic Drugs.<ref>{{Cite journal | vauthors = Riboulet-Zemouli K, Krawitz MA, Ghehiouèche F |date=2021 |title=History, Science, and Politics of International Cannabis Scheduling, 2015–2021 |url=https://papers.ssrn.com/abstract=3932639 |journal=FAAAT editions |language=en |location=Rochester, NY |ssrn=3932639 |via=SSRN}}</ref>

==Society and culture== ===Brand names=== Dronabinol is marketed as Marinol and Syndros,<ref>EMCDDA, ELDD Comparative Study, May 2002.</ref> a registered trademark of Solvay Pharmaceuticals. Dronabinol is also marketed, sold, and distributed by PAR Pharmaceutical Companies under the terms of a license and distribution agreement with SVC pharma LP, an affiliate of Rhodes Technologies for Marinol and Insys Pharmaceuticals for Syndros.{{citation needed|date=March 2016}} Dronabinol is available as a prescription drug (under Marinol and Syndros)<ref>{{cite web|url=http://www.usdoj.gov/dea/ongoing/marinol.html |archive-url=https://web.archive.org/web/20021021154502/http://www.usdoj.gov/dea/ongoing/marinol.html |archive-date=21 October 2002 |title=Marinol – the Legal Medical Use for the Marijuana Plant |publisher=Drug Enforcement Administration |access-date=20 April 2011}}</ref> in several countries including the United States, Germany, South Africa and Australia.<ref>{{cite web | work = Alchimia Blog | url = http://www.alchimiaweb.com/blogen/marijuana-and-medicine-cesamet-marinol-sativex/ | archive-url = https://web.archive.org/web/20160220112337/http://www.alchimiaweb.com/blogen/marijuana-and-medicine-cesamet-marinol-sativex/ | archive-date = 20 February 2016 | title = Marijuana and Medicine: Cesamet, Marinol, Sativex }}</ref> In Canada, Tetra Bio-Pharma filed a New Drug Submission (NDS) with Health Canada for its Dronabinol Soft Gel capsules to be marketed as Reduvo.<ref>{{cite web | date = 30 December 2020 | work = AP News | url = https://apnews.com/press-release/accesswire/business-science-corporate-news-north-america-products-and-services-36f832c5b3802082fac1531ed879cda5 | title = Tetra Bio-Pharma Files New Drug Submission for REDUVO™ in Canada }}</ref> Tetra has two other dronabinol drugs with new routes of administration which limit first-pass metabolism; an inhaled THC-based dronabinol drug and their mucoadhesive-delivery dronabinol drug Adversa, which are both in the accelerated 505(b)(2) New Drug Application (NDA) pathway for the U.S. and Canadian markets.<ref>{{cite web | work = Tetra Bio-Pharma | date = 16 December 2020 | url = https://ir.tetrabiopharma.com/newsroom/press-releases/news-details/2020/Tetra-Bio-Pharma-Acquires-Exclusive-Global-Technology-Rights-to-a-Mucoadhesive-Delivery-Technology-Called-AdversaR-for-its-PPP-002-dronabinol-drug-candidate-from-IntelGenx/default.aspx | title = Tetra Bio-Pharma Hits Another Milestone Before Year End: Inhaled Dronabinol & MucoAdhesive Dronabinol 'Adversa' | access-date = 2 January 2021 | archive-date = 26 November 2020 | archive-url = https://web.archive.org/web/20201126035657/https://ir.tetrabiopharma.com/newsroom/press-releases/news-details/2020/Tetra-Bio-Pharma-Acquires-Exclusive-Global-Technology-Rights-to-a-Mucoadhesive-Delivery-Technology-Called-AdversaR-for-its-PPP-002-dronabinol-drug-candidate-from-IntelGenx/default.aspx }}</ref>

In the United States, Marinol is a Schedule III drug, available by prescription, considered to be non-narcotic and to have a low risk of physical or mental dependence. Efforts to get cannabis rescheduled as analogous to Marinol have not succeeded thus far, though a 2002 petition has been accepted by the DEA. As a result of the rescheduling of Marinol from Schedule II to Schedule III, refills are now permitted for this substance. Marinol's U.S. Food and Drug Administration (FDA) approval for medical use has raised much controversy<ref>{{cite web|url=http://blog.sfgate.com/smellthetruth/2014/10/21/war-on-marijuana-unconstitutional-doctors-testify-in-federal-court-monday/|title=War on marijuana unconstitutional, doctors testify in federal court Monday|access-date=21 October 2014|date=21 October 2014| vauthors = Downs D |publisher=sfgate.com|archive-date=22 October 2014|archive-url=https://web.archive.org/web/20141022140851/http://blog.sfgate.com/smellthetruth/2014/10/21/war-on-marijuana-unconstitutional-doctors-testify-in-federal-court-monday/}}</ref> as to why cannabis is still illegal at the federal level.<ref>{{cite web | vauthors = Eustice C |url= http://arthritis.about.com/cs/medmarijuana/a/marijuanadebate.htm |title=Medicinal Marijuana: A Continuing Controversy |publisher=About.com |date=12 August 1997 |access-date=20 April 2011 |archive-date=15 June 2011 |archive-url=https://web.archive.org/web/20110615031136/http://arthritis.about.com/cs/medmarijuana/a/marijuanadebate.htm }}</ref>

==Comparisons with medical cannabis== {{Further|Medical cannabis}}

Female cannabis plants not only contain THC but at least 113 other cannabinoids,<ref>{{cite journal | vauthors = Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = Journal of Natural Products | volume = 79 | issue = 2 | pages = 324–31 | date = February 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 | bibcode = 2016JNAtP..79..324A | url = https://figshare.com/articles/journal_contribution/5028338 | url-access = subscription }}</ref> including cannabidiol (CBD), thought to be the major anticonvulsant that helps people with multiple sclerosis;<ref name="pmid6269680">{{cite journal | vauthors = Pickens JT | title = Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content | journal = British Journal of Pharmacology | volume = 72 | issue = 4 | pages = 649–56 | date = April 1981 | pmid = 6269680 | pmc = 2071638 | doi = 10.1111/j.1476-5381.1981.tb09145.x }}</ref> and cannabichromene (CBC), an anti-inflammatory which may contribute to the pain-killing effect of cannabis.<ref name=Burns2006>{{cite journal | vauthors = Burns TL, Ineck JR | title = Cannabinoid analgesia as a potential new therapeutic option in the treatment of chronic pain | journal = The Annals of Pharmacotherapy | volume = 40 | issue = 2 | pages = 251–60 | date = February 2006 | pmid = 16449552 | doi = 10.1345/aph.1G217 | s2cid = 6858360 }}</ref>

It takes over one hour for Marinol to reach full systemic effect,<ref>{{DailyMed|41006|MARINOL (dronabinol) capsule}}</ref> compared to seconds or minutes for smoked or vaporized cannabis.<ref name="mckim">{{cite book | vauthors = McKim WA |title=Drugs and Behavior: An Introduction to Behavioral Pharmacology |edition=5th |publisher=Prentice Hall |year=2002 |page=[https://archive.org/details/drugsbehaviori00mcki/page/400 400] |isbn=978-0-13-048118-4 |url-access=registration |url=https://archive.org/details/drugsbehaviori00mcki/page/400 }}</ref> Mark Kleiman, director of the Drug Policy Analysis Program at UCLA's School of Public Affairs said of Marinol, "it wasn't any fun and made the user feel bad, so it could be approved without any fear that it would penetrate the recreational market, and then used as a club with which to beat back the advocates of whole cannabis as a medicine."<ref name="Respectable Reefer">{{cite news|url=http://motherjones.com/politics/2005/11/respectable-reefer|title=Respectable Reefer| vauthors = Greenberg G |date=1 November 2005|access-date=8 April 2010|publisher=Mother Jones}}</ref>

Clinical trials comparing the use of cannabis extracts with Marinol in the treatment of cancer cachexia have demonstrated equal efficacy and well-being among subjects in the two treatment arms.<ref name="urlCannabis and Cannabinoids (PDQ) – National Cancer Institute">{{cite web | url = http://www.cancer.gov/cancertopics/pdq/cam/cannabis/healthprofessional/page5 | title = Cannabis and Cannabinoids (PDQ) | publisher = National Cancer Institute, U.S. Department of Health and Human Services | work = Cancer Topics | date = 2011-03-16 }}</ref> United States federal law currently registers dronabinol as a Schedule III controlled substance, but all other cannabinoids remain Schedule I, except various synthetic cannabinoids like nabilone and HU-308.<ref>{{cite web |url=http://onlineathens.com/stories/070399/new_pot.shtml |title=Government eases restrictions on pot derivative |publisher=Online Athens |access-date=12 January 2014 |archive-url=https://web.archive.org/web/20141216134540/http://onlineathens.com/stories/070399/new_pot.shtml |archive-date=2014-12-16 }}</ref><ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. |access-date=2021-01-10 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm }}</ref>

The FDA has recognized that there can be cannabinoid impurities in pharmaceutical dronabinol including cannabinol, Δ8-tetrahydrocannabinol, isotetrahydrocannabinol, and Δ11-tetrahydrocannabinol.<ref>{{Cite web |date=28 June 2016 |title=Pharmacology Review - Syndros |url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000PharmR.pdf |archive-url=https://web.archive.org/web/20220227043927/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000PharmR.pdf |archive-date=February 27, 2022 |website=Food and Drug Administration |publisher=Center for Drug Evaluation and Research}}</ref><ref>{{Cite web | vauthors = Jian H, Dilek I, Sreenivasan U, Yaser K |date=2010 |title=Investigation of the Impurities in Dronabinol Samples by LC/MS |url=https://www.cerilliant.com/shoponline/OpenDocument.aspx?DocumentID=38 |website=Cerilliant}}</ref>

==See also== {{portal|Cannabis|Chemistry}} * Cannabinoids ** 11-Hydroxy-THC, metabolite of THC ** Anandamide, 2-Arachidonoylglycerol, endogenous cannabinoids ** Tetrahydrocannabinol ** Cannabidiol (CBD) ** Cannabinol (CBN), a metabolite of THC ** Dimethylheptylpyran ** Parahexyl ** Tetrahydrocannabinolic acid, the biosynthetic precursor for THC ** HU-210, WIN 55,212-2, JWH-133, synthetic cannabinoid agonists (neocannabinoids) * Medical cannabis (pharmaceutical cannabinoids) ** Epidiolex (prescription form of purified cannabidiol derived from hemp used for treating some rare neurological diseases) ** Sativex (nabiximols) ** Nabilone, a novel synthetic cannabinoid ** HU-308, a highly potent synthetic cannabinoid CB2 receptor agonist ** Zenivol (ZTL-101)

==References== {{Reflist}}

==External links== * [https://medlineplus.gov/druginfo/meds/a607054.html Medlineplus.gov on Dronabinol]

Category:Acetylcholinesterase inhibitors Category:Amorphous solids Category:Antiemetics Category:Appetite stimulants Category:Aromatase inhibitors Category:Benzochromenes Category:Drugs developed by AbbVie Category:Entheogens Category:Euphoriants Category:Social problems in medicine Category:Tetrahydrocannabinol